4 Ways to Wear Checkerboard Vans in 2024 (Plus One Way that Dates You Immediately)

According to a fashion editor who’s obsessed

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how to wear checkerboard vans CAT
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Earlier this year Associate Fashion Commerce Editor Stephanie Meraz made the prediction that checkerboard Vans—the black-and-white slip-on sneaker that was so ubiquitous in the early aughts—would soon replace Adidas Sambas as the shoe of the summer. And, reader, I am happy to report that she was right on the money. The throwback shoe is everywhere I look, and I for one couldn’t be more excited. I’ve loved these shoes since high school, viewing them as the epitome of cool (which at the time involved pretty much any style associated with the skaters and surfers of Southern California). That said, the attention-grabbing style isn’t quite as easy to wear as a plain white sneaker. Read on for four easy to recreate outfit ideas, all featuring checkerboard Vans, plus one ‘fit you’re better off skipping in 2024.

I Tested lululemon's Newest (Under $100) Summer Staple at a Business Meeting, the Beach & the Airport

how to wear checkerboard vans with solid colors
Abby Hepworth

1. Mix and Match Solid-Colored Separates

A bold black-and-white checkerboard print is already enough of a scene stealer, don’t make it compete with a ton of other colorful patterns. Instead, try creating your own colorblocked ensemble (as I did above) with solid-colored pieces in a range of hues. The end result is fun, cheery and still lets your shoes be the center of attention.

how to wear checkerboard vans with denim midi skirt
Abby Hepworth

2. Swap Denim Shorts for a Denim Midi Skirt

Denim shorts and an easy tee is a fine enough summer outfit, but if you want to dress up your skater-approved Vans I suggest swapping those cutoffs for an elevated denim midi skirt. Use other accessories, like chunky gold hoops, a sleek leather belt and a timeless shoulder bag to further zhuzh up the trendy sneaker.

how to wear checkerboard vans with prints and patterns
Abby Hepworth

3. Choose a Print or Pattern That Incorporates Black and White

If you do want to try mixing prints, start with just one and make sure it has pops of black and white in the mix. This ensures the two patterns have at least one connecting thread and won’t look totally in contrast with one another. Keep your accessories minimal, however—less is more when you’re already working with multiple bold pieces.

how to wear checkerboard vans with little black dress
Abby Hepworth

4. Try a ‘90s-Inspired LBD

Minimalist ‘90s styles are another hot trend for summer 2024, and luckily for you makes for a perfect balance to sporty, kitschy checkerboard sneakers. Try pairing your kicks with a little black dress inspired by Rachel Green or Carrie Bradshaw for a look that’s subtly cool and 100 percent on trend. (I’m definitely wearing this one to dinner and drinks with friends.) Lean into the ‘90s minimalism for your accessories as well, with pearl earrings and a simple leather shoulder bag.

how not to wear checkboard vans
Abby Hepworth

5. Don’t: Go Ham with Prints

Piling on all the colorful prints and patterns ends up reading very early 2000s, and not necessarily in a good way. Brightly colored solids are a much more modern option that still gives you the ability to make a big statement with your outfit.



Abby Hepworth is an RRCA-certified running coach who has worked in fashion for over 10 years. Want to know what shoes are in this season? She's got you. Need recommendations on...

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